but rate the albums fevers and mirrors>lifted>letting off the happiness>wide awake = digital ash>peoples key> cassadaga but all of them have some amazing moments, all the eps are great too

im wide awake its morning is quite indie rock depressing rating 7/10
fevers and mirrors is more acoustic but not really folk, has an ornate harmonic minor sound hard to describe and is him at his most dramatic and self aware depressing ratin 10/10
lifted has a ramshackle big band folk sound with some cinematic touches, quite epic and hopeful depressing rating 4/10
im wide awake is simple acoustic songs with some perfect arrangements depressing rating 4/10
digital ash mixes in synths and drum machines for some really good dark atmospheric sounds and some less successful upbeat electro indie pop depressing rating 6/10
cassadaga, sounds like lifted but slicker and not as good depressing rating 4/10
the peoples key, sounds like the less succesful parts of digital ash but they also said they wanted to go for a non reggae reggae sound which you can kinda of hear with the tape echos and other effects, its interesting but they lyrics are abit cryptic I dont know what he is singing about anymore depressing scale unknown

The most accessable straight up indie/country/folk record would be wide awake followed by lifted. They're both excellent records so are good jumping on points.
If you want more like that then pick up Cassadega.

For early more lo-fi Bright Eyes, Fevers and Mirrors is one of the most mature teenage she dumped me records you'll hear, cos ultimatly thats what it is, but it's got fantastic arrangements and lyrics that transend that.
If you like that then go to Letting of the Happiness and if you want even more lo-fi then Collection of Songs... but that is a bit fans only as he was about 14/15 when he made it.

For other more electronicy Bright Eyes; Digital Ash, which is fantastic but maybe not quite as accessable. The one I seem to go back to most nowadays.
Then People's Key, the new one which is also brilliant and some people say it's his masterpiece. And it could be but not a starting point I feel.